I have a multiple-entry one-year Schengen visa and I did have travel insurance first time when I crossed the border of Schengen, but it has expired already and I wonder if I need it during my next trips to Europe?

Is this something that you are obliged to have or it's ok not to have it?

Are you talking about crossing internal borders between two Schengen countries, or about crossing external borders, entering Schengen from a non-Schengen country, or exiting from a Schengen country to a non-Schengen country?
–
hippietrailFeb 10 '13 at 2:05

2 Answers
2

Technically yes, the terms under which a Schengen visa is issued require you to have health insurance up to a certain amount of coverage. You may be asked for proof of this in the form of health insurance documents when you're entering the Schengen zone and/or at any passport control checks.

In practice though, it is unlikely that you will be asked to provide documentation for this. However, travel health insurance is still a good thing to have as hospitalisation costs in case something does happen can be expensive. You don't need to get an expensive policy; at least in the UK, you can get short term travel health policies which cost less than £10. Even though these policies may have high deductibles, for serious accidents they will still help you recover medical expenses.

I'm travelling between EU and UK every week for the last six months. Never been asked for health insurance once. However, it's safer to have it. That's why it's called accident and insurance. In case, something unthinkable situation happens.
–
toyFeb 11 '13 at 13:49

I have never been asked for that on European Airports Check points.
They usually ask you

Where you're going

What you're going to do

How long you will stay. Sometimes they even ask you to show them your returning back tickets or reservation.

I once saw a police asking a person to show him how much money this person got. It really depends on how the police look at you…

However, travel insurance is a requisite to enter a Schengen country. In fact, it is stated in every European embassy webpage. It costs about $50 USD for two weeks covering $50,000 USD. I believe you should spare no expense. No one ever knows.

Almost at the bottom of the Wikipedia article on the Schengen area, there is a table of procedures border guards follow when checking travellers who cross external borders of the Schengen area.